The first JumpStart game, the 1994 version of JumpStart Kindergarten, was released in 1994. From that time up to 1998, grade-based games were added to the JumpStart series: JumpStart Preschool and JumpStart 1st Grade in 1995; JumpStart 2nd Grade, JumpStart 3rd Grade, JumpStart 4th Grade (1996 version), and JumpStart Pre-K in 1996; JumpStart 5th Grade and JumpStart Toddlers in 1997; JumpStart 6th Grade in 1998; and JumpStart Baby in 1999. Other games, which were either based on a single skill or a subject combined with a grade level, were also released during this time (circa 1997): JumpStart Kindergarten Reading, JumpStart 1st Grade Math, JumpStart 1st Grade Reading, JumpStart 2nd Grade Math, JumpStart Typing, and JumpStart Spanish. (In 2000, JumpStart Kindergarten Reading was renamed to JumpStart Reading for Kindergarteners, JumpStart 1st Grade Math was renamed to JumpStart Math for First Graders, JumpStart 1st Grade Reading was renamed to JumpStart Reading for First Graders, and JumpStart 2nd Grade Math was renamed to JumpStart Reading for Second Graders. Also, JumpStart Math for Kindergarteners and JumpStart Reading for Second Graders were released at this time.) Three games, JumpStart Spelling, JumpStart Music, and JumpStart Numbers (called "Learning Games" because they were somewhat more focused on arcade gameplay) were also released around this time.

Each of the original grade-based games contained its own setting and cast of characters, completely separate from all other JumpStart games (though occasionally characters would cameo in other grade levels' games), though JumpStart Pre-K is an exception to this rule, featuring the characters from JumpStart Preschool. The games which were not solely grade-based each used a set of characters from one of the main grade-based games; the characters never mixed at this time, and as far as the grade-based-and-subject-based games are concerned, which set of characters featured in each game was quite logical (i.e. Frankie the dog appeared in JumpStart 1st Grade, JumpStart Reading for First Graders, and JumpStart Math for First Graders). The games which were not solely grade-based often made updates to the character designs of the characters they featured; for example, in JumpStart 1st Grade, Frankie the dog had cartoonish proportions and wore nothing but a blue collar; changes were made to his character designs in future games, including more normal proportions and a red vest.

From about 1998-2000, significant upgrades were made to several of the games (namely JumpStart Kindergarten in 1998, JumpStart Preschool in 1999, JumpStart 1st Grade in 2000, JumpStart 4th Grade in 2000, and JumpStart Toddlers[3] in 2000; notably, the updates to Preschool, Kindergarten and 1st Grade were significant, but the games still had many similarities to their predecessors, while Toddlers and 4th Grade were updated into entirely new games that did not even feature the same characters). Even for the games that weren't updated, new boxarts were devised.

Starting circa 1999, a significant change was brought on in the JumpStart series, under the leadership of their Creative Director Marcela Cabrera,[4] who re-developed the new vision of the brand and produced the new visual identity of the software language : several of the characters (the main characters of JumpStart Preschool, Kindergarten, 1st Grade, and 2nd Grade) were given redesigns and merged into a single continuity in which they interacted with each other. This started with the release of two 30-minute animated videos, JumpStart Preschool (occasionally subtitled "Who Left Their Juice on the Caboose?") and JumpStart Kindergarten (occasionally subtitled "Why Did the Bus Stop?"), and JumpStart ABC's and JumpStart Phonics (both of which were part of the same "Learning Games" series than included JumpStart Spelling, Music, and Numbers). The JumpStart Preschool VHS and the JumpStart ABC's game were clearly meant to tie into each other, as were the JumpStart Kindergarten VHS and the JumpStart Phonics game. The "Learning Game" JumpStart Phonics should not be confused with the entirely different JumpStart Phonics that was released around the same time and featured a different premise in the same continuity. (The non-Learning Game was originally released as a part of a collection known as the JumpStart Phonics Learning System,[5] and was also released separately.[6])

In 2001, each of the original grade-based games received a boxart redesign and a bonus disc was added to each. JumpStart Baby (which was actually updated significantly, unlike the other games which simply received new boxarts) received JumpStart Baby Book,[7]JumpStart Toddlers received My Learning Scrapbook,[8] the games for Preschool-2nd Grade each received JumpStart Around the World and the games for 3rd Grade-6th Grade each received Adventure Challenge. (For each grade, the version included was slightly different.) JumpStart Pre-K was not re-released, however. (It is worthy to note that Adventure Challenge featured a continuity containing characters from JumpStart 3rd Grade-6th Grade, as a counterpart to the many games released during this era that featured characters from JumpStart Preschool-2nd Grade.)

The JumpStart workbook series and the JumpStart Readers series, both published by Scholastic, were also released at this time. They, and all the games released from 2001 until 2005, featured slightly updated character designs as compared to such games as JumpStart ABC's and JumpStart Phonics. Each series contained entries for Pre-K, Kindergarten, 1st Grade, and 2nd Grade. As far as the workbooks were concerned, even though the updated designs of the characters were used, characters only appeared in workbooks for the grade level that they appeared in back in the classic grade-based games; i.e. C.J. Frog and Edison Firefly, who appeared in the original JumpStart 2nd Grade, were the only characters to appear in the 2nd Grade workbooks. This is not the only instance that, despite the characters having been mostly merged into one canon, the "specific characters for a grade level" theme appeared in the second era. For example, one of the ways in which the different grade-level versions of Around the World were different was in which characters were your "travel buddies" and most prominently featured.

Even in some products which featured characters from multiple grade levels, vestiges of the "old system" could be seen; for example, frequently the JumpStart Readers would include characters from many grade levels, but the characters who were once the main characters of that grade level's game starred prominently.

In 2001, more non-grade based-games were released that were sometimes referred to on the back of their boxes as "Early Discovery" games. These included JumpStart Artist (which taught various aspects of art), JumpStart Languages (which taught Spanish, French, and Japanese), JumpStart Explorers (which taught various subjects, mostly history), and JumpStart Animal Adventures (which taught zoology). Also, two games for older children, JumpStart SpyMasters: Unmask the Prankster and JumpStart Spy Masters: Max Strikes Back were released. Similarly to JumpStart Adventure Challenge, these games featured a continuity containing characters from JumpStart 3rd Grade, JumpStart 4th Grade (2000), JumpStart 5th Grade, and JumpStart 6th Grade.

In 2002, four completely new grade-based games - JumpStart Advanced Preschool, JumpStart Advanced Kindergarten, JumpStart Advanced 1st Grade, and JumpStart Advanced 2nd Grade - were released. These featured, among other things, a gimmick known as the "All-Star", in which at the beginning of the game, a user may choose (or answer a personality quiz to automatically determine) a character which represents a "Learning Style" based on the theory of multiple intelligences. These characters were Casey the Cat the athlete (represents bodily-kinesthetic learning), C.J. the Frog the scientist/naturalist (represents naturalistic learning), Eleanor the Elephant the reader (represents linguistic learning), Frankie the Dog the team leader/"people person" (represents interpersonal learning), Hopsalot the Rabbit the Math Whiz (represents logical-mathematical learning), Kisha the Koala (represents visual/spatial learning), and Pierre the Polar Bear the musician (represents musical/auditory learning). Throughout most of the game, a star would appear in the lower-right corner of the screen. This star could be clicked at any time to display a "walkie-talkie" that allows the user to access brief videos based around each learning style/character on any subject matter in the game, defaulting to the subject being taught by the activity currently being played and the learning style selected by the user. (The All-Star also pops up automatically if the user chooses wrong answers repeatedly.) Edison the Firefly is also featured, but not on the walkie-talkie.

In 2003, the entire grade-based JumpStart series (even those which were not actually updated in 2002) were released under the JumpStart Advanced label in new packages which each contained 3 discs. Also in 2003, JumpStart Study Helpers Math Booster and JumpStart Study Helpers Spelling Bee were released. Both of them have an editor feature that allows users to enter their own lists of spelling words or math problems to use during gameplay.[9][10]

In 2005, JumpStart Reading with Karaoke (which was renamed JumpStart Phonics Read & Rhyme in 2006[11]) was released. It featured a new continuity with new (and in the case of several of the characters, very different) character designs, to the extent that two of the characters, Pierre and Kisha, were reimagined as entirely different animals (Pierre Polar Bear became a panda and Kisha Koala became a cheetah). Also significant of this continuity was the absence of the characters Casey Cat and Edison Firefly.

In 2007, the JumpStart World (later renamed JumpStart 3D Virtual World) games were released: JumpStart World Kindergarten,[12][13]JumpStart World 1st Grade,[14] and JumpStart World 2nd Grade.[15] These games featured online connectivity, gameplay that took place primarily in an three-dimensional environment, and other features. Each package came with two units of play, and the rest could be obtained via an $8/month membership.

Though JumpStart World became the main product in the JumpStart line, new packages of the JumpStart Advanced series with four discs were made. Circa 2008, a factory error caused some of these packages to erroneously contain a different game listed as Fundamentals than the original.

In 2008, the JumpStart World products were updated into new JumpStart Advanced Premium packages, which included a brand-new Preschool title.[16][17]

On December 1, 2008, a JumpStartmassively multiplayer online game, which would go on to become the series' main product, was announced, with StoryLand (for 3-5 year olds) being one of the first areas released.[18] It was launched on March 10, 2009, with the inclusion of an additional world, AdventureLand, for a somewhat older audience.[19] This game, geared for ages 3–10, features customizable avatars called "Jumpeez". Many other areas have since been added to JumpStart, such as MarineLand and FutureLand.[20] MarineLand is targeted towards intermediate ages (5-9) and FutureLand is geared toward the upper end of the JumpStart age spectrum.

The JumpStart.com MMOG, similar to its predecessor JumpStart World, features an $8/month membership. It is not necessary to play the game, but to access certain features.

FutureLand features Dr. Brain, a character who appeared in other (non-JumpStart) educational products in the past and is owned by Knowledge Adventure.

Starting in 2012, JumpStart began releasing products (including features in their online game and apps) that featured Dreamworks Animation properties, such as Madagascar and How to Train Your Dragon.

Although JumpStart was originally a series of personal computer games, other educational products have been produced under the JumpStart name. For example, a large collection of books (with the majority being workbooks) have been created by a cooperative effort between Knowledge Adventure and Scholastic.[21] They have been manufactured for 4 grade levels: Pre-K, Kindergarten, first grade, and second grade. The workbooks feature characters from the particular grade level, though another kind of JumpStart book, "JumpStart Readers" (storybooks intended to teach reading skills) sometimes feature characters from other grade levels. The workbooks also feature a sticker reward system and offer "tips".

There have also been multiple JumpStart games produced for systems other than the PC and Mac; JumpStart Dino Adventure for the Game Boy Color, JumpStart Wildlife Safari for the PlayStation and three JumpStart Wii games; JumpStart Pet Rescue, JumpStart: Escape from Adventure Island, and JumpStart Get Moving Family Fitness.

4 JumpStart DVD games (JumpStart Frankie's Field Trip,[22]JumpStart Power Prep 2nd Grade, JumpStart Power Prep 3rd Grade and JumpStart Power Prep 4th Grade), known as "iDVDs", have also been made by Knowledge Adventure.

Several JumpStart apps for the iPad (some of which can also be played on the iPhone) have been created - JumpStart Preschool: Magic of Learning,[23]JumpStart Punk Punk Blitz,[24]JumpStart Jetpack,[25]JumpStart My ABC Book,[26]JumpStart Art Studio,[27] and JumpStart Roller Squash.[28] JumpStart Preschool: Magic of Learning received critical acclaim[29] and was also published for Windows Phone.[30][31]

A few JumpStart toys have also been produced.

In March 2014, it was announced that JumpStart had purchased Neopets from Viacom.